Amino acids and peptides. Part 19. Synthesis of β-1- and β-2-adamantyl aspartates and their evaluation for peptide synthesis
Amino acids and peptides. Part 19. Synthesis of β-1- and β-2-adamantyl aspartates and their evaluation for peptide synthesis
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DOI：
10.1039/p19880002129
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发表时间：
1988
期刊：
影响因子：
--
通讯作者：
Y. Okada;S. Iguchi
中科院分区：
文献类型：
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作者：
Y. Okada;S. Iguchi
本文合成了β-1-和β-2-金刚烷基丙酸酯[H-Asp（O-1-Ada）-OH和H-Asp（O-2-Ada）-OH]，并对其性质进行了研究。虽然1-Ada基团对TFA不稳定，但2-Ada基团在TFA处理期间不受影响，但在室温下5 min内可通过甲磺酸（MSA）轻松去除。在易于从α-氨基上裂解芴-9-基甲氧羰基（Fmoc）的条件下，用55%哌啶处理两个基团均不受影响。这两个基团都可以抑制天冬酰亚胺的形成，这是合成天冬酰肽过程中酸性和碱性条件下的副反应。β-1-或β-2-金刚烷基戊酸酯分别与Fmoc或Boc作为Nα-保护基组合可用于固相肽合成。描述了天冬酰胺部分的一些性质。
β-1- and β-2-Adamantyl aspartates [H-Asp(O-1-Ada)-OH and H-Asp(O-2-Ada)-OH] have been synthesized and their properties examined. Although the 1-Ada group is labile to TFA, the 2-Ada group is unaffected during TFA treatment, but easily removable by methanesulphonic acid (MSA) at room temperature within 5 min. Both groups are unaffected by treatment with 55% piperidine under conditions which easily cleave the fluoren-9-ylmethoxycarbonyl (Fmoc) group from an α-amino group. Both groups can suppress aspartimide formation as a side reaction under acidic and basic conditions during the synthesis of aspartyl peptides. β-1-or β-2-Adamantyl aspartates may be applicable to solidphase peptide synthesis in combination with Fmoc or Boc as an Nα-protecting group, respectively. Some properties of the aspartimide moiety are described.